72995-94-9

Basic information

• Product Name: 14-Bromotetradecanol
• Synonyms: 14-BROMO-1-TETRADECANOL;14-BROMO-TETRADECAN-1-OL;14-BROMOTETRADECANOL;1-Tetradecanol, 14-bromo-
• CAS NO: 72995-94-9
• Molecular Formula: C₁₄H₂₉BrO
• Molecular Weight: 293.28
• Product Categories: pharmacetical
• Mol File: 72995-94-9.mol

Chemical Properties

• Melting Point: 42-43 °C(Solv: heptane (142-82-5))
• Boiling Point: 353.6 °C at 760 mmHg
• Flash Point: 131.1 °C
• Appearance: /
• Density: 1.084 g/cm³
• Vapor Pressure: 2.05E-06mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.20±0.10(Predicted)
• CAS DataBase Reference: 14-Bromotetradecanol(CAS DataBase Reference)
• NIST Chemistry Reference: 14-Bromotetradecanol(72995-94-9)
• EPA Substance Registry System: 14-Bromotetradecanol(72995-94-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 72995-94-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
14-Bromotetradecanol is used as a synthetic intermediate for the production of cyclohexenoic long chain fatty alcohols, which have potential applications as neuronal growth stimulators. These stimulators can promote the growth and development of neurons, offering potential therapeutic benefits for neurological disorders and injuries.
Used in Chemical Synthesis:
14-Bromotetradecanol can also be utilized as a starting material or building block in the synthesis of other complex organic compounds. Its unique structure and reactivity make it a valuable component in the development of new pharmaceuticals, agrochemicals, and specialty chemicals.

InChI:InChI=1/C14H29BrO/c15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16/h16H,1-14H2

Upstream product

• 19812-64-7 1,14-tetradecanediol 
• 5024-21-5 dimethyl tetradecanedioate 
• 821-38-5 1,14-tetradecanedioic acid 

Downstream Products

• 402483-49-2 1,1-(ethylenedioxy)-3-(14-hydroxytetradecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane 
• 321155-32-2 1-(15-hydroxypentadecyl-1-phenylsulfonyl)-2,6,6-trimethyl-1-cyclohexene 
• 211443-83-3 16,16,17,17,18,18,18-d7-stearic acid 
• 907218-92-2 14-(2,5-dimethoxyphenylamino)tetradecan-1-ol 
• 907218-96-6 [14-(tert-butyl-dimethyl-silanyloxy)-tetradecyl]-(2,5-dimethoxy-phenyl)-amine 
• 887604-06-0 hexadec-15-ynyloxymethyl-benzene 
• 887604-26-4 Q₂FA₁₆ 
• 887604-31-1 Q₃FA₁₆ 
• 887604-11-7 2-(16-Benzyloxy-hexadec-1-ynyl)-1,4-dimethoxy-benzene 
• 887604-16-2 1-(16-Benzyloxy-hexadec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-21-9 1-(16-Benzyloxy-hexadec-1-ynyl)-2,3,4,5-tetramethoxy-benzene 
• 310869-77-3 3-[4-(14-hydroxy-tetradecyloxy)-benzyl]-4H-[1,2,4]oxadiazol-5-one 
• 850143-28-1 4-(14-(tetrahydropyran-2-yloxy)tetradecyloxy)benzyl cyanide 
• 850143-47-4 4-(14-(tetrahydropyran-2-yloxy)tetradecyloxy)phenylacetamidoxime 

Relevant articles and documents

Discovery and Pharmacological Studies of 4-Hydroxyphenyl-Derived Phosphonium Salts Active in a Mouse Model of Visceral Leishmaniasis

We report the discovery of new 4-hydroxyphenyl phosphonium salt derivatives active in the submicromolar range (EC50 from 0.04 to 0.28 μM, SI > 10) against the protozoan parasite Leishmania donovani. The pharmacokinetics and in vivo oral efficacy of compound 1 [(16-(2,4-dihydroxyphenyl)-16-oxohexadecyl)triphenylphosphonium bromide] in a mouse model of visceral leishmaniasis were established. Compound 1 reduced the parasite load in spleen (98.9%) and liver (95.3%) of infected mice after an oral dosage of four daily doses of 1.5 mg/kg. Mode of action studies showed that compound 1 diffuses across the plasma membrane, as designed, and targets the mitochondrion of Leishmania parasites. Disruption of the energetic metabolism, with a decrease of intracellular ATP levels as well as mitochondrial depolarization together with a significant reactive oxygen species production, contributes to the leishmanicidal effect of 1. Importantly, this compound was equally effective against antimonials and miltefosine-resistant clinical isolates of Leishmania infantum, indicating its potential as antileishmanial lead.

Chemoenzymatic macrocycle synthesis using resorcylic acid lactone thioesterase domains

A key missing tool in the chemist's toolbox is an effective biocatalyst for macrocyclization. Macrocycles limit the conformational flexibility of small molecules, often improving their ability to bind selectively and with high affinity to a target, making them a privileged structure in drug discovery. Macrocyclic natural product biosynthesis offers an obvious starting point for biocatalyst discovery via the native macrocycle forming biosynthetic mechanism. Herein we demonstrate that the thioesterase domains (TEs) responsible for macrocyclization of resorcylic acid lactones are promising catalysts for the chemoenzymatic synthesis of 12- to 18-member ring macrolactones and macrolactams. The TE domains responsible for zearalenone and radicicol biosynthesis successfully generate resorcylate-like 12- to 18-member macrolactones and a 14-member macrolactam. In addition these enzymes can also macrolactonize a non-resorcylate containing depsipeptide, suggesting they are versatile biocatalysts. Simple saturated omega-hydroxy acyl chains are not macrocyclized, nor are the alpha-beta unsaturated derivatives, clearly outlining the scope of the substrate tolerance. These data dramatically expand our understanding of substrate tolerance of these enzymes and are consistent with our understanding of the role of TEs in iterative polyketide biosynthesis. In addition this work shows these TEs to be the most substrate tolerant polyketide macrocyclizing enzymes known, accessing resorcylate lactone and lactams as well as cyclicdepsipeptides, which are highly biologically relevant frameworks.

Highly efficient preparation of selectively isotope cluster-labeled long chain fatty acids via two consecutive Csp3-Csp3 cross-coupling reactions

An efficient synthesis involving two copper-catalyzed alkyl-alkyl coupling reactions has been designed to easily access doubly isotope-labeled fatty acids. Such NMR- and IR-active compounds were obtained in excellent overall yields and will be further used for determining the conformation of an alkyl chain of lipidic biomolecules upon interaction with proteins.

Viscosalines B1,2 and E1,2: Challenging new 3-alkyl pyridinium alkaloids from the marine sponge Haliclona viscosa

Four new 3-alkyl pyridinium alkaloids, the viscosalines B1 (1 a), B2 (1 b), E1 (2 a), and E2 (2 b), were isolated from the Arctic sponge Haliclona viscosa. The structure elucidation of these isomeric compounds was challenging due to ambiguous fragments that derive during "standard" mass spectrometric fragmentation experiments. The final structure elucidation relied on the use of a combination of synthesis, liquid chromatography, and mass spectrometry. Three different mass spectrometers were used to differentiate between the synthetic structural isomers: a time-of-flight (TOF) mass spectrometer and two ion-trap mass spectrometers with different ion-transfer technologies (i.e., skimmer versus funnel optics). Although at first none of the spectrometers returned spectra that permitted structure elucidation, all three mass spectrometers provided analysis that successfully differentiated between the isomers after thorough method optimization. The use of in-source collision-induced dissociation (CID) with the ion trap and TOF instrument returned the most interesting results. The mode of fragmentation of the viscosalines under different experimental conditions is described herein. After successful optimization of the mass spectrometric method applied, the chromatographic method was improved to distinguish the previously inseparable isomers. Finally, both the liquid chromatography and mass spectrometric methods were applied to the natural products and the results compared to those from the synthetic compounds. Copyright

Hydroxylated Long-Chain Resveratrol Derivatives Useful as Neurotrophic Agents

The present invention relates to a compound of general formula (I) below in which R1, R2 and R3 represent, independently of one another, a hydrogen atom or a C1-C6 alkyl group or a (C1-C6 alkyl)carbonyl group, R4, R5, R6 and R7 represent a hydrogen or a C1-C6 alkyl group, a C1-C6 alkoxy group or a (C1-C6 alkyl)carbonyloxy group, and n is an integer between 8 and 20, or its pharmaceutically acceptable addition salts, isomers, enantiomers and diastereoisomers, and also mixtures thereof. The invention also relates to a pharmaceutical composition comprising the compound and to the use thereof as a neurotrophic agent.

First syntheses of model long-chain trichloro[ω-(trimethylsilyl)alkynyl]silanes suitable for self-assembled monolayers on silicon surfaces

The preparation of the title compounds involves the introduction of the required Me3SiC{triple bond, long}C and trichlorosilyl groups at the termini of the alkyl chain via derivatization of easily accessible and inexpensive materials/reagents. Trichloro[ω-(trimethylsilyl)alkynyl]silanes are useful for the linkage to a hydroxylated silicon surface for multilayer formation and for further chemical modification of the tail group of the monolayer.

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The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).

HYDROQUINONE LONG-CHAIN DERIVATIVE AND/OR PHENOXY LONG-CHAIN DERIVATIVE, AND PHARMACEUTICAL PREPARATION COMPRISING THE SAME

The present invention provides compounds represented by formula (1) shown below: (wherein R1, R2, R3, R4, and R5 are each individually selected from among a hydrogen atom, methyl group, acetyl group, hydroxyl group, and alkoxy group; and X represents an alkylene group or alkenylene group); and compounds represented by formula (2) shown below: (wherein R6, R7, R8, R9, and R10 are each individually selected from among a hydrogen atom, alkyl group, acetyl group, hydroxyl group, and alkoxy group; A represents an oxygen atom or NH, and m is 0 or 1; and Y represents an alkylene group or alkenylene group, and Z represents a hydrogen atom or hydroxyl group).The compounds of the present invention are useful for preventing or treating brain dysfunctions, motor dysfunctions, or urinary dysfunctions caused by the degeneration and/or loss of the central nervous system or peripheral nervous system cells.The present invention provides compounds represented by formula (1) shown below: (wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each individually selected from among a hydrogen atom, methyl group, acetyl group, hydroxyl group, and alkoxy group; and X represents an alkylene group or alkenylene group); and compounds represented by formula (2) shown below: (wherein R 6 , R 7 , R 8 , R 9 , and R 10 are each individually selected from among a hydrogen atom, alkyl group, acetyl group, hydroxyl group, and alkoxy group; A represents an oxygen atom or NH, and m is 0 or 1; and Y represents an alkylene group or alkenylene group, and Z represents a hydrogen atom or hydroxyl group). The compounds of the present invention are useful for preventing or treating brain dysfunctions, motor dysfunctions, or urinary dysfunctions caused by the degeneration and/or loss of the central nervous system or peripheral nervous system cells.

Solid-phase synthesis of quinol fatty alcohols, design of N/O-substituted quinol fatty alcohols and comparative activities on axonal growth

Following the promising activity of Q2FA15 on axonal growth, two new series of N/O-substituted QFAs were synthesized, based on a SN2-type reaction. O-alkylated QFA bearing 14 carbon atoms on the side chain (n = 14) shows a very potent activity on axonal growth though lowered when compared to Q2FA15. While O-alkylation allows good retention of the biological activity, N-alkylation abolishes it nonetheless. A solid-phase-supported synthesis of Q2FA15 allowing the conception of new hybrid compounds is also described.

Quinol fatty alcohols as promoters of axonal growth

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